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Puerto Rico Cruises Starting In October 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in October 2027 or 2028, we have 23 unique cruise itineraries and 108 departures available, operated by seven of the world's leading cruise lines departing in October.
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23 Cruises (108 Departures)
23 Cruises (108 Departures)
Departures
Duration
8 Days
20 Days
Countries Visited
Start & End Cities
Ship Size
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Operators
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Price
$700pp
$28,620pp
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13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (2)

13 Days (12 Nights) Barcelona to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visits: Spain, Morocco, Puerto Rico
Drinks On Us
Inside
$1,752
Oceanview
$1,752
Balcony
$1,930
Suite
$6,535
From (Per Person)
A$1,752
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$977
Oceanview
$1,106
Balcony
$1,264
Suite
-
From (Per Person)
A$977
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$1,561
Oceanview
$1,888
Balcony
$2,175
Suite
-
From (Per Person)
A$1,561
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$715
Oceanview
$873
Balcony
$1,170
Suite
$2,309
From (Per Person)
A$715
Save 16
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$865
Oceanview
$895
Balcony
$1,142
Suite
$1,736
From (Per Person)
A$865
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visits: Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$878
Oceanview
$1,046
Balcony
$1,204
Suite
-
From (Per Person)
A$878
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Operator: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$2,059
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$2,059
Save 1,035
Per Person
View Trip
10 Day New York to San Juan with Crystal Cruises
New ReleaseCruise

10 Days (9 Nights) New York to San Juan
Operator: Crystal
Ship: Crystal Symphony
Departure: 26 October 2026
Visits: USA, Bermuda, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$5,092
Balcony
$5,872
Suite
$6,262
From (Per Person)
A$5,092
Save 1,608
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departures: Oct 2026 to Oct 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,545
Oceanview
$1,821
Balcony
$2,023
Suite
$4,472
From (Per Person)
A$1,545
Save 1,152
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Jun 2027 to Oct 2027
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,555
Oceanview
$1,609
Balcony
$1,746
Suite
$3,961
From (Per Person)
A$1,555
Save 1,214
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 17 October 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,202
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,202
Save 180
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
$1,928
Balcony
$2,225
Suite
$9,554
From (Per Person)
A$1,928
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (6)

10 Days (9 Nights) New York to San Juan
Operator: Azamara
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,805
Oceanview
$1,995
Balcony
$3,981
Suite
$6,813
From (Per Person)
A$1,995
Save 34
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,047
Oceanview
$1,109
Balcony
$1,689
Suite
$2,312
From (Per Person)
A$1,047
Save 904
Per Person
View Trip
20 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

20 Days (19 Nights) Genoa to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
$2,315
Oceanview
-
Balcony
$2,830
Suite
-
From (Per Person)
A$2,315
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$10,658
From (Per Person)
A$10,658
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visits: Italy, Spain, Portugal, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
$2,028
Balcony
$2,344
Suite
$10,156
From (Per Person)
A$2,028
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visits: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,562
Oceanview
$2,869
Balcony
$3,413
Suite
$5,779
From (Per Person)
A$2,562
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Drinks On Us
Inside
$1,230
Oceanview
$1,332
Balcony
$1,436
Suite
-
From (Per Person)
A$1,230
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,177
Oceanview
$1,246
Balcony
$2,309
Suite
$3,053
From (Per Person)
A$1,177
Save 690
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 23 October 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,796
Oceanview
$1,947
Balcony
$2,027
Suite
$4,176
From (Per Person)
A$1,796
Save 963
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$925
Oceanview
$1,143
Balcony
$1,192
Suite
$1,687
From (Per Person)
A$925
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,521
Oceanview
$1,593
Balcony
$1,832
Suite
$5,724
From (Per Person)
A$2,443
Save 40
Per Person
View Trip
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